Flirting With the Enemy
by starcrossedloversofmysticfalls
Summary: In the mob world, the biggest rivalry has always been between the Salvatore's and the Gilbert's. But what happens when Stefan Salvatore falls for a brown haired, doe eyed girl without knowing that she's a Gilbert just when he's about to take on the family business?


**Hey guys! This is my first story and I know this first chapter might seem a little rushed and short but I promise that the chapters after this are going to be much longer and get more into everything about Stefan, Elena, why the families hate each other, etc. just bare with me! I hope you guys like it!**

* * *

In his mere nineteen years of life, he'd never seen someone as breathtakingly stunning as her. He'd been watching her from across the room the whole night, unable to build up enough to courage to go over and talk to her. This had never happened to him before – he never had trouble striking up a conversation with a beautiful girl. It's not like he was a womanizer – that would be the worst adjective to describe Stefan Salvatore. Of course, he had been in relationships before, but none of them ever lasted more than a couple of months. The mysterious brunette had a different vibe about her than the usual type of girls that Stefan went after, though. He couldn't put his finger on it, but something, or everything, about this girl intrigued him. Stefan chugged the last few sips of his beer before slamming his bottle on the bar and walking over to the brunette that he had been captivated by all night. She was with a couple of other girls and it was times like these when Stefan wished that his brother was the same age as him so that he could have him be his wingman and distract the brunette's friends while Stefan focused all of his attention this girl. His roommate, Nik, who usually took over the wingman duties when Stefan found a girl that he'd like to find out more about, decided to stay in and study instead of going out, so, Stefan was on his own for the night.

"Hello, ladies," Stefan greeted the three girls as he walked up to their table with a genuine smile formed on the corners of his lips.

The three girls all shared glances with one another before looking over at Stefan before one of the mysterious brunette's friends answered, "May we help you?"

He shrugged his shoulders slightly. "I just thought I'd introduce myself to the three most beautiful girls in the bar. I'm Stefan," he told them as his green eyes averted to the brunette, "and you are?"

"Not interested in being your next one night stand," the brunette shot right back at him with a hint of disgust in her voice.

"Well, well, well. Didn't your mother ever tell you to not judge a book by its cover?" Stefan asked, cocking his head.

"I know your type," she told him instantly, "You introduce yourself to us, hang out for a little bit, ask one of us to go somewhere a little bit more private, we have sex, give you our number, and then we never hear from you again. And I can promise you that neither myself or my friends are interested in that."

A look of confusion mixed with hurt washed over Stefan's face. He'd never had a one-night stand in his life. "So, since I called the three of you beautiful, that automatically makes me a douchebag who would use you and then never call you or talk to you ever again? Did you ever think that I was just being nice? And honest? Not every guy that you come across is like that, you know. You shouldn't assume things about people before you actually get to know them, " Stefan explained before shaking his head slightly and letting out a quiet sigh. "Have a nice, ladies," he said sincerely before turning around and walking back to the bar to order another drink.

* * *

Stefan sat at the bar with a glass of bourbon in his hand, taking a swig every once in a while. He heard someone sit next to him and he looked up to find the brunette sitting next to him. He furrowed his brows in confusion as his eyes locked with hers.

"Elena," she said softly, "My name is Elena."

"And here I thought your name was not interested," Stefan said with a light laugh, "Where'd your friends go?"

"They were tired and decided to head back to our dorm room and call it a night. But, I decided to stay out a little bit longer and maybe actually get to know you instead of just judging," she explained as small smile forming on the corners of her lips. Stefan was sure that her smile could light up the whole college, if need be. He'd never seen a smile as beautiful as hers.

"Well, can I buy you a drink?" Stefan asked her and Elena shook her head 'yes'. He ordered her the same drink that she had been drinking when he approached her earlier.

The two of them sat at that bar for hours just talking. They talked about school, books, movies, where they were from. It turned out that they only lived twenty minutes away from each other and went to rival high schools. Stefan wasn't satisfied, though. He wanted to know more. He wanted to know everything about Elena. It was as if she was a drug and he was addicted. Her laugh and her smile were already imprinted in the back of his mind. Every aspect of Elena intrigued him – how she was so quick to reject him earlier to protect herself and her friends when she thought that Stefan was planning on using one of them for sex, how she was an English major and sent out her first manuscript a week earlier, how her eyes lit up when Stefan told her he wanted to read her story, how her laugh was contagious and he was sure that he could listen to it for hours and never get bored.

Stefan walked her back to her dorm room since their dorms were only a couple of buildings apart. Even though she told him she would be able to make it back to her dorm just fine, Stefan insisted. He wanted to spend as much time with her as possible. They reached her building sooner than Stefan expected and he felt a twinge of disappointment in the pit of his stomach.

"Well, this is my stop," Elena pulled out the swipe key to unlock her dorm room building. She turned around to face Stefan, "Thank you for walking me back to my dorm."

"It was my pleasure. So…" Stefan's voice trailed off, "I guess I'll see you around then?"

Elena nodded her head, confirming that he'd see her again. Her infamous smile formed on her lips again as she pulled out a piece of paper and scribbled her number on it. "Here," she said, handing him the piece of paper, "Goodnight, Stefan," Elena waved slightly as she opened the door to her building. As soon as the door closed behind her, Stefan grinned from ear to ear. He pulled out his phone and immediately saved Elena's number. His grin dropped slightly when he realized he hadn't gotten her last name, but he could just find that out another time.

He opened up his dorm room door to find Nik passed out with his history book on his face, causing Stefan to shake his head and chuckle. He tossed his leather jacket onto his desk chair and kicked his shoes off. Stefan grabbed a pair of sweats and put them on after taking his jeans off. Before Stefan got into bed, he peeled his t-shirt off since it could get ridiculously hot in the dorm rooms at night. He pulled his sheets over his body and closed his eyes as he rested his head on his pillow. The second his eyes closed he could see Elena's smile – the smile that was unforgettable. Before he knew it, he was drifting off to sleep with only one thing on his mind – Elena.

* * *

"Stefan! Come on! We're going to be late!" Damon, Stefan's older brother, yelled from their living room.

"I'm coming! I'll be downstairs in two minutes!" Stefan called out from his bedroom, which was on the opposite side of the infamous Salvatore Boarding House.

Stefan was nineteen years old now, which meant that he had to begin helping with the Salvatore family business – taking down the Gilbert's. This would be his first time on the job with his brother and they were crashing a Gilbert family party along with the rest of the Salvatore family and everyone that worked for the Salvatore's. Stefan was only really able to work on the weekends since he was going to school at Whitmore College, which was a good two-hour drive away from his hometown. He grabbed his jacket and slipped it on as he walked down the stairs.

"It's about time, little brother," Damon greeted, "Ready for your first real job in the Salvatore family business?"

"I was born ready, Damon," Stefan replied to his older brother with confidence and a smug smile plastered on his face. The two brothers walked out to the cars and they both sat in the backseat.

"The party is for the Gilbert's daughter. It's being held at the Mystic Grill so they won't be able to kick us out," Damon explained and Stefan just shook his head to let his brother know that he was listening. The younger Salvatore would be lying, though, if he said that it wasn't easy to keep his mind on track. Ever since last night, the only thing, or person, that Stefan could think about was Elena. He had to wake up early to drive back home to crash the Gilbert's party, but he figured he could call Elena on his way back up to Whitmore and see if she would like to go out to a late dinner.

The car came to a stop and Stefan took a deep breath as he stepped out of the car. This was it. This was the moment when he would finally become like his father, uncle, brother, and cousins and start working for the mob. He knew it was dangerous – but he couldn't just stop family tradition. Once you turn 19 in the Salvatore family, taking down the rival mob family practically becomes your life. Luckily, Stefan's father, Giuseppe, allowed him to go to school, as well as working for him. If he didn't go to school at Whitmore, he wouldn't have met Elena last night. Plus, Stefan actually enjoyed school – he loved learning something new every day. Even though with his soon-to-be profession, that had been lined up for him since before he was born, none of the material that he was learning in college would ever be useful to him.

The Salvatore's opened the doors to the Mystic Grill and made their entrance. Stefan followed behind Damon, since he was just going to be shadowing his older brother throughout the whole party. It all felt like such a thrill. He hadn't even been on the job for more than two minutes and he could feel the adrenaline rushing through his veins.

"What are you doing here, Salvatore?" An older man asked Damon, the annoyance and disgust clear in his voice.

"Oh, we just heard you were having a little party and decided to stop by," Damon replied with a smug smirk on his face.

"If you ruin this party for my daughter, Salvatore, I swear to god I will have a bullet through your forehead before you have any idea what's even happening," the man, who Stefan figured was Grayson Gilbert, warned before walking away from the two brothers.

Stefan patted his older brother on the back and continued to walk around the Mystic Grill. He ordered himself a beer from the bartender when he heard Grayson telling everyone to be quiet and that she was almost here. A look of confusion washed over Stefan's face – _hadn't the party already started?_, he thought to himself, but then it hit him. It was a surprise party for the Gilbert's daughter.

Stefan followed Damon as the two made their way to middle of the crowd that was forming in the center of the Mystic Grill. A smirk formed on Stefan's lips as he waited for the daughter to enter the Grill. He couldn't wait to start reeking havoc because the sooner the Salvatore's did what needed to be done, the sooner Stefan could get back into his car and drive back up to Whitmore, and hopefully see Elena.

Two girls that looked very familiar entered the Mystic Grill rather quickly – Stefan recognized them. He saw them at the bar last night, they were Elena's friends. _How do Elena's friends know the Gilberts?_, he thought to himself again. Stefan's once smug smirk quickly dropped and his green eyes grew wide when he saw a brunette walk into the Mystic Grill. Everyone accept the Salvatore's yelled, "Surprise!" but Stefan drowned out the cheers. Shock had overcome him and he couldn't take his eyes off of her. She is apart family that he and his family have hated and have been set on destroying for as long as he can remember.

"Elena…" Stefan said to himself, barely above a whisper.


End file.
